Ethanol → 4,5-Dimethyl-1,2-phenylenediamine

HRID 1781031Notes

Reaction equation

HRID 1781031 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7](C)[C:5]([NH2:6])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[CH2:13](O)C>[Pd]>[NH2:6][C:5]1[CH:7]=[C:8]([CH3:13])[C:2]([CH3:1])=[CH:3][C:4]=1[NH2:10]

Participants

4

Reactant 2

HCID 702EthanolHCID 742196-Nitro-2,4-xylidine

Product 1

HCID 766354,5-Dimethyl-1,2-phenylenediamineYield 96%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 4,6-dimethyl-2-nitroaniline (1.66 g, 10.0 mmole) and 10% Pd/C (200 mg) in ethanol (35 mL) was hydrogenated for 2 h at room temperature under 25 psi H2. The catalyst was removed by filtration with celite and the solvent was removed by rota-evaporation to give 1.300 g (96%) of 1,2-diamino-4,5-dimethylbenzene as a brown solid. 1H NMR (CDCl3): 6.449 (s, 1H), 6.469 (s, 1H), 3.327 (br, 2H), 3.259 (br, 2H), 2.190 (s, 3H), 2.159 (s, 3H).

Workup

  1. customThe catalyst was removed by filtration with celite
  2. customthe solvent was removed by rota-evaporation

Sources & evidence

ORD record
ord-101ba999a0e442b7a1ebad51b3339ed1
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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